


Deep Filled

by ficforthought



Category: Supernatural
Genre: Bottom Jack Kline, Cock Slut Jack Kline, Double Anal Penetration, Established Relationship, M/M, Mention of Bottom Sam Winchester, Mention of Weecest, Polyamory, Threesome - M/M/M, Under-negotiated Kink
Language: English
Status: Completed
Published: 2020-11-02
Updated: 2020-11-02
Packaged: 2021-03-09 02:07:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,182
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27356989
Author URL: https://archiveofourown.org/users/ficforthought/pseuds/ficforthought
Summary: Jack can't get enough of Sam and Dean filling him up, so the brothers decide to take it to a new level.
Relationships: Dean Winchester/Sam Winchester, Jack Kline/Dean Winchester, Jack Kline/Dean Winchester/Sam Winchester, Jack Kline/Sam Winchester
Comments: 21
Kudos: 135





	Deep Filled

Dean blinks into awareness, the remnants of the night’s sleep leaving him slowly. He lets out a small contented noise as he rolls his hips, pressing his morning wood into the supple ass it’s pressed up against. Jack must have somehow turned over in his sleep, quite an achievement since he and both brothers are currently all squeezed into the same double bed. Now instead of being the little spoon in Sam’s embrace, the Nephilim is moulded to Dean’s front, exactly how the hunter likes it because being the big spoon makes him feel like he’s looking after his boys, even in sleep.  
  
It’s clear from the steady breaths that both of them are sound asleep, so he props himself up on one elbow and takes in the sight before him. The sheets are crumpled down at the bottom of the bed where one or all of them had kicked them off in the night, so he doesn’t even have to fight with them to be able to look over the full length of his brother and their adopted son and lover.  
  
Sam is wearing his favoured long sleeved grey top which Dean also loves because the v-neck perfectly accentuates his brother’s long neck and throat, and dark blue bottoms which pull snug over his muscular ass and thigh where his leg is raised, knee around Jack’s thigh and his foot resting on Dean’s shin. One hand is wrapped loosely around the back of Jack’s head and the other resting half on Dean’s chest and half on the kid’s upper arm. Jack is dressed in worn, pale blue pinstripe pyjama bottoms and a soft, once white t-shirt which hangs loose over his slim frame, sliding off his shoulder where the neckline is stretched out on one side where Sam likes to tug it down and kiss the kid’s collarbone. He has one hand under his own cheek and the other around Sam’s waist, with his head tucked under the younger Wincester’s chin, forehead pressed into the hollow of Sam's clammy throat. Both of them look calm, relaxed, somehow open and vulnerable which is Dean’s mind means that at same time they look absolutely sinful and desirable, too.  
  
When he shifts position slightly so he can lean closer to them both, the dim lights of the bunker highlight the contours of Sam’s angular face, Jack’s body and the contrast between them. Sam being the Sasquatch he is, broad shoulders and long legs taking up most of the bed, and Jack’s slimmer, shorter frame allowing him to curl even smaller in the space left. Seeing him so small and fragile looking - despite him being anything but - makes Dean want to hold the kid and protect him from the world and from his own powers. A small part of him thinks he should be protecting Jack from the brothers Winchester, too...he and Sam know this relationship isn’t healthy, neither is the one they’ve had for years, either, but it works for them so fuck what everyone else thinks. Family is the most important thing, and the way they express their love is nobody else’s business but their own.  
  
The older man is drawn from his musings when Sam’s breathing changes slightly. Dean’s hands itch to touch, so as carefully as he can he sits up and strokes Sam’s cheekbone with the back of his hand, the light stubble he feels there scratching him in the best way. A couple more times and his baby brother’s eyes flicker open, “Morning, sunshine,” he says in half whisper, cupping Sam’s jaw and stroking his cheek with a thumb.  
  
Sam frowns a little and makes a small noise of protest like he’s made since he was kid when he’s been gently woken up. Dean finds incredibly endearing, but he’d never admit it in a million years, “Hey,” the younger man replies, voice sleep rough and sexy as fuck, “you’re awake early.”  
  
Dean shrugs, “Who says it’s not you that’s awake late?” he teases, smiling softly at the inevitable eye roll it earns him, but Sam still angles his head so he’s leaning in to his brother’s touch. When the hand on Dean’s chest grips his t-shirt and gently tugs he goes with it, leaning in to press a soft kiss to Sam’s lips, the slow drag of it feeling lazy and indulgent.  
  
“Jack?” Dean whispers when they pull apart, but there’s no response. He’s not deterred, though, sliding his hand from Sam’s face down to Jack’s belly, slipping it under his t-shirt to touch smooth, sleep warmed skin, “C’mon, baby boy, wake up,” he whispers into the shell of Jack’s ear. He traces the contours of the kid’s torso, scratching lightly over the skin of his hip then over a flat nipple. Heavy eyelids flicker ever so slightly at that, long eyelashes fanned out over pale skin. Without another word, Dean leans back over towards Sam to take his lips in another slow kiss, but this time slips in his tongue.  
  
His baby brother moans into it, then a little louder and from the slight movement of the bed Dean can tell he’s rolling his hips, pressing his dick against Jack’s hip. There’s another small sound, this time from Jack when Dean rubs the pad of his fingers over Jack’s nipple before gently pinching it between his thumb and forefinger. He does it again, still sweeping his tongue into Sam’s mouth, this time earning himself a breathy moan from the kid, who’s finally starting to stir.  
  
The slick sound of the brothers’ lips parting seems to bring Jack more into wakefulness, a contented sigh coming from him as he snuggles further into the body in front of him for a moment like he’s trying to hold on to sleep, before he raises his head to blink blurrily up at Sam, “What’s going on?” he asks, rubbing one eye and although Dean can’t actually see it, he knows from the soft look on his brother’s face that the kid looks fucking adorable.  
  
Sam’s answer is wordless, sliding his hand into the kid’s hair and pulling him closer to pepper kisses over his cheeks and nose before capturing those soft pink lips with his own. He rolls his hips into Jack’s body and it’s firm enough to push the kid against Dean, who in turn rocks against the pliant body in front of him, the older man letting out a small moan when the Nephilim presses himself back against the full length of Dean’s body.  
  
Sam releases his grip on his brother’s t-shirt in favour of palming Dean’s ass cheek, pulling so that they’re even closer together, grinding a little firmer before he moves the hand to rest on Jack’s hip. He breaks the kiss with Jack and immediately leans over towards his brother, lips slick and swollen, face flushed and Dean eagerly slips his tongue back into Sam’s mouth to taste the combination of him and Jack.  
  
“Dean...” Jack moans as the hunter rubs and tugs on his nipples, alternating between the two, “please,” he whispers, words slightly slurred from still not being fully awake.  
  
Sam breaks the kiss and looks down at Jack with a smirk on his face. From the corner of his eye Dean sees his brother’s large hand slide from the kid’s hip into the space between their bodies, and from the way Jack gasps and rocks his hips it’s clear Sam’s rubbing his cock through the cotton of his pyjamas.  
  
“Hmm?” Dean hums against the skin at the nape of Jack’s neck, trailing kisses along his hairline and sucking slightly behind the kid’s ear until it earns him an involuntary moan and shiver. He slides his hand down the Nephilim’s body until he can cover Sam’s hand with his own, applying more pressure until the Jack moans again. Dean looks over at his brother, “What do you think our boy here wants, Sammy?” he says, lips ghosting over the shell of Jack’s ear, again.  
  
Sam grins but says nothing, squeezing the kid’s cock and slowly stroking him. Dean knows from experience how much Sam likes to tease, so he also knows the pressure will be enough to heat their young lover’s blood but not to bring him proper relief, so he removes his hand from Sam’s and slides it under the waistband of Jack’s pants and pushes the fabric down enough to expose the top of the kid’s ass. He splays his fingers half over the Nephilim’s hip, his thumb ghosting over the crease of his thigh in half a promise of what’s to come.  
  
“I think he wants you to kiss him, right Jack?” Sam coos, lifting the kid’s chin and angling his head towards Dean. The position can’t be comfortable but Jack twists as much as he can, slick pink mouth parted in anticipation, offering the older man a half smile and nods.  
  
“Yeah?” Dean says, leaning further over so that he can press his lips to Jack’s. They’re swollen, hot and pillowy soft. The kid is the first to use tongue, still a little uncertain as he presses it gently against Dean’s, hot and soft, pressure and confidence increasing when a breathy sigh falls from the older man’s lips. The bed shifts as Sam moves and pushes Jack’s pyjamas down, tapping his thigh and encouraging him to lift his hip so they can be pushed off. The kid breaks the kiss to manoeuver so that he can kick them free. Dean uses the opportunity to rid himself of his boxers and t-shirt while Sam pulls shirt Jack’s off, turning him again so that his back is along Dean’s front again.  
  
Jack lets out a frustrated sound which indicates Sam isn’t naked quick enough, reaching out in an effort to help, but he ends up gripping the cotton in his fist when Dean presses a kiss to his shoulder and dips his fingers between the kid’s cheeks, rubbing over his slick hole.  
  
“Mmm,” Dean hums into his skin as he looks over at his brother, “he’s still wet, Sammy, we put real good loads into him last night, huh?”  
  
Sam smiles down at Jack, thumb rubbing the kid’s bottom lip, “Sure did, just like he wanted, right, Jack?”  
  
“Yes,” the Nephilim replies, nodding eagerly, “always want you both in me,” he says around Sam’s thumb as he slips it into the kid’s mouth.  
  
“Mmm, such a greedy hole, never quite full enough for you, is it?” Dean says, raising his eyebrow in Sam’s direction, his brother’s reply a small shrug and an amused smile. It’s true, the boy never seems more content than when they take it in turns to fill him from both ends, “Well let's see what we can do about that, sweetheart,” the older man says, adjusting the angle of his wrist so he can press two fingers against Jack’s hole, applying only slight pressure, humming in approval when the tips slip straight inside him with barely any resistance. The slick, burning heat makes him groan, “Jesus, Sammy, he’s still loose, too, bet I could slip right in there without any more prep.”  
  
They all moan as Dean pushes in further, Jack’s muscles fluttering around his fingers, rolling his hips in an attempt to take more. Always wanting more, they’re learning.  
  
“Look at you, so eager,” Sam says, voice deep with lust, “can’t wait to be filled up again, can you?” Jack shakes his head but says nothing, panting and letting out a pleading whine as Sam reaches around and slowly slides a finger in alongside Dean’s, “ _Fuck_ , Jack,” he says, cut off when the kid’s lips slam back against his.  
  
“That’s the plan,” Dean chuckles, driving his fingers deeper inside Jack’s heat, “Sammy, get the lube.” The younger man pulls out of the kiss with a questioning sound but says nothing as Dean throws a look his way that tells him to do as he’s told. Dean sucks kisses all along Jack’s neck and shoulder while he pumps steadily into the kid, adding a third finger soon after and stretching him with little effort. Jack lets out a whimper, “You OK there, kiddo?” he asks, stilling his fingers, the last thing he wants to do is hurt their boy.  
  
The Nephilim nods, turning back to look at Dean and the hunter groans at the sight. The kid is already flushed, eyes glazed with lust and looking desperate from what they’ve done so far, “Please, Dean,” he croaks, “want you.”  
  
Sam groans from the other side of the bed, “Always so greedy for Dean’s cock aren’t you, baby boy?” he licks his lips and looks between Jack and his brother, his own flushed face full of want, “There’s nothing quite like it, feels so good being split open by it, right? I can’t get enough, either!” he admits.  
  
Heat floods through Dean’s body knowing that all these years later Sam still feels that way, “He’s right,” he rasps into Jack’s ear, pumping and spreading his fingers even wider, “shoulda seen him in his teens, totally desperate for it all the damn time,” he rubs firmly over that spot inside Jack just to feel his body jerk and tighten and to hear him moan, “just like you’re becoming, sweetheart. My perfect little cock slut.”  
  
“I wasn’t _that_ desperate,” Sam argues, “and I was fourteen, dude, I was perpetually horny, it goes with the territory.”  
  
“And perpetually climbing me like a fucking tree,” Dean laughs, winking at his brother, “not that I was complaining, of course.”  
  
“Damn right!” Sam replies with a sly grin before looking back down at Jack, “You ready for more?”  
  
Jack lets out a frustrated noise, rolls his hips back and grabs Sam’s giant hand in his, guiding it down his body to his cock. From the strangled moan it’s obvious Sam is thumbing the head in just the way Jack likes, “Yesss, come on,” he hisses.  
  
“How can we refuse that?” Dean says, tipping his chin back encouraging Sam to come closer. They share a kiss that’s mostly tongue before he pulls away and whispers into his baby brother’s ear, “lots of lube, work him open as much as you can, OK?”  
  
Sam draws back, a small look of confusion on his face before understanding registers, eyes flicking to Jack’s flushed face then back to his brother, “Yeah,” he nods, eagerly, “yeah, OK.”  
  
Jack makes a whining noise that puts any puppy Dean’s ever heard to shame, “Hurry _up_ ,” he begs, “want you inside me.”  
  
Sam laughs, softly, “So needy,” he says, quickly ridding himself of his pyjamas, coating his fingers with lube and bringing them around to Jack’s hole. The kid squirms as the long digits rub the slick around his rim and Dean’s fingers when he slides them out. A deep groan escapes the older Winchester as he feels one of Sam’s fingers slide in beside his own, pumping in counterpoint and panting almost as hard as Jack is, “feel so good in there, Jack,” Sam says, brushing the kid’s sweaty hair from his forehead with his free hand.  
  
Jack squirms some more as Dean slides his fingers out and presses the head of his cock against the kid’s stretched hole alongside Sam’s finger, “Ready, sweetheart?” he asks, needlessly. Jack’s never once refused this, but every time they ask just to make sure. The Nephilim came to them that first time, red faced, asking to experience what it was that had Sam crying out in pleasure the night before. After some initial reservations on the brothers’ part it was ultimately too appealing to pass up and now there’s no going back unless Jack asks them to stop, but since he only seems to get needier all the time, it’s highly unlikely. It’s been months and none of them can get enough, and for Dean in particular, being granted permission never gets old.  
  
“Son of a-,” Jack huffs, “ _I’m ready_ , stop teasing and fill me up.”  
  
“Fuck, gonna do exactly that, baby boy, fill you like you’ve never been filled before,” Dean says around a groan as the head of his cock slides inside Jack, the slick of the lube and their combined come making it easy to push all the way in with one push.  
  
Jack lets out a deep, satisfied moan at the feeling, his sweaty hand reaching back to scrabble over Dean’s thigh, “Gah, _finally_!” he pants, grinding his hips back to try and take Dean in deeper.  
  
“God, Jack,” Sam says, leaning in close enough to almost kiss while he curls his finger to stretch the kid open more, “who knew you were going to be so cock hungry?” He looks over at his brother with a smirk before licking into Jack’s mouth while he works his finger as deep as he can inside.  
  
“Sammy,” Dean says, purposefully keeping his thrusts slow, barely pulling out, loving the frustrated sounds coming from the Nephilim’s mouth at not getting what he wants yet, “get to work.” The pair part with a slip pop, Jack’s hand leaving Dean’s thigh to reach for Sam’s head in an attempt to keep the kiss going but the younger brother has already moved out down to his chest, kissing his way downwards. Dean angles his body so he can place an awkward kiss to Jack’s lips before kissing down his jaw and nuzzling behind his ear. He reaches out to roll one of the kid’s nipples between finger and thumb, trying to distract him from what’s coming. Another of Sam’s fingers rest against Jack’s rim, the back of his knuckles brushing against Dean’s balls and the older man stills his hips, “just relax,” he says into Jack’s sweaty skin when the pressure around his dick increases as his brother’s fingers pushing in alongside it.  
  
Jack whimpers slightly, not anticipating the stretch, but that was the point, “Shh, ‘s’alright,” Sam coos, “let me in,” the words spoken around him pressing sloppy kisses to what Dean assumes is the younger man’s belly and hips, “gonna make you feel good.” There’s a muffled moan from Sam as he takes Jack’s cock into his mouth and the kids hips buck frantically, muscles squeezing tighter around Dean’s dick.  
  
“Fuck, easy, kid, easy,” Dean pants, trying not to buck his own hips, “you like the way Sammy sucks your cock, right?” Jack's answer is an affirmative sound from the back of his throat as the wet sucking sounds get louder from where Sam’s working more enthusiastically. Jack’s ass flutters, drawing another moan from all three of them.  
  
The older hunter shifts his body so the arm propping him up slips under Jack’s neck, holding him close while the other hooks under the kid’s knee, spreading him out more. Sam looks up at the change in position, meeting his brother’s eyes, soft pink mouth still full of their boy’s dick. They both nod and Dean rolls his hips slightly as Sam’s fingers press tighter together before he slips a third inside Jack’s stretched hole, pressing all the way in slowly but steadily.  
  
“Fuck,” Jack says, slim body rocking as he grips the sheets with one hand and grips Sam’s shoulder with the other, “what are you doing?” he asks with a shaky voice.  
  
“Shh,” Dean says into the sweaty hair at the nape of Jack’s neck, “you wanted filling up, that’s what we’re doing,” he presses a kiss to the flushed skin, “do you want to stop?”  
  
Jack takes a couple of deep breaths and lets his body relax, “No, keep going,” he says, followed by another moan as Sam pumps his fingers in a counter rhythm to Dean’s hips. They keep that up until Jack seems to relax around them even more and Sam slips a fourth finger inside. The Nephilim tenses up again then, letting out a small wounded sound but immediately rolls his hips to push back onto the fingers and cock inside him.  
  
“Jesus, Jack,” Sam pants after he pulls off their boy’s dick, working his fingers in at a steadier pace, “you look so fucking hot like this,” he spreads his fingers a little wider, twisting his wrist to get a better angle and pumps more firmly, opening the kid up as much as he can, “wish you could both see this.”  
  
“Tell us,” Dean rasps, unable to stop himself thrusting into Jack a little faster, earning a moan of pleasure from the Nephilim.  
  
The bed shifts as Sam gets up on his knees so he’s towering over both of them. He’s flushed and sweaty, cheeks and lips bright pink as he looks between Jack’s hole and his two lovers, “Pretty hole stretched so wide over us, Dean,” Sam says, voice low and rough, “pinky white just...here,” they both jerk when Sam’s thumb brushes over Jack’s rim then the base of Dean’s dick, “how does it feel, Jack?”  
  
Their young lover’s breath hitches and Dean slams into him again, “Good, so good,” he sobs, “need more.”  
  
Dean huffs out a laugh, “ _More_? Sammy, I think you were right,” a hard thrust, his hips slamming against Jack’s perky cheeks, “his hole is so greedy,” he plucks one of Jack’s nipples and earns himself a whine and clench of internal muscles, “think you can really take more?”  
  
“Y-yes!” Jack cries, answering just as Sam opens his fingers wider, “Sam, please, more.”  
  
Sam’s answering moan and slick sound tells Dean that his little brother is stroking himself with the hand not stuffed inside the kid, “Fuck, yeah, alright,” he says, letting go of his cock and very slowly sliding his fingers out of Jack’s ass.  
  
Their boy protests vocally and with his body, muscles fluttering and trying to hold Sam’s fingers inside him but it’s too late, “No, please,” he sobs, “Sam, you said…”  
  
He’s cut off by Sam's lips slamming into his, manhandling him so he’s half sat up before he breaks the kiss, “Dean, pull out,” he says urgently, “gotta move into a better position.”  
  
“Aww, come on, man,” Dean says, aware he’s whining but not caring. The last thing he feels like doing is giving up that exquisite heat he’s buried in, but he does it anyway, carefully slipping out because Jack may be stretched but he’s probably a little sore and the older man doesn’t want to hurt him by going too quickly. He and Sam have talked about the possibility of this, but now it’s here he’s going to be extra careful.  
  
Somehow Jack gets up on hands and knees, looking between them with a look of desperation on his face, eyes lust blown, sweaty bed hair stuck up in all directions, “Why did you stop, did I do something wrong?” he rasps.  
  
“Not at all, baby, just got something we think you’ll like better,” Sam replies, reaching out to take hold of Jack’s upper arm, tugging him closer as he positions himself against the headboard, guiding Jack to straddle his hips. He cradles Jack’s head in one of his huge hands and pulls him in for a deep kiss full of tongue, both of them moaning into it. He pats the Nephilim’s thigh with his free hand, encouraging him to raise up on his knees enough for Sam to position the head of his cock against Jack’s puffy, gaping hole. Dean groans like he’s the one being filled as he watches his brother sinking inside their boy, fucking up into the kid several times before the older hunter walks closer on his knees.  
  
“Come on...” Jack says around a groan as he works his hips against the older man, following it up with a small gasp-whimper combo as Sam jerks the kid’s cock a few times.  
  
Dean positions himself so that he’s in between Sam’s legs, hands on Jack’s slim hips, chest firmly against his back, pressing open mouthed kisses to the kid’s shoulder and neck. He looks over at his brother, holding his gaze for a few seconds before Sam nods again and a fresh wave of arousal burns through Dean’s body, they’re finally doing this.  
  
“Lean forward, sweetheart,” he says into Jack’s ear, his heart beating faster as the boy immediately obeys, “that’s it. Just relax and enjoy this, let us take care of you,” he says as he slips pointer and middle fingers straight inside that fluttering heat.  
  
Jack gasps, pushing back to meet the intrusion, “Dean,” he moans, a plea and a prayer at the same time, he lifts his head and leans forward a little more, “Sam…” he rasps, then there’s the slick sound of them kissing again.  
  
Dean uses the temporary distraction to push his little finger into Jack’s heat and tug at the rim, holding him open enough to rest the head of his cock against it, the slick slide of Sam’s shaft against him making Dean shiver until his brother holds still. Very slowly Dean presses forward until there’s a give of muscle and he slips inside, gently withdrawing his fingers at the same time. Jack’s body goes rigid and he gasps as he pulls out of the kiss with Sam, “Shh, we got you,” Dean coos, pushing inside agonisingly slowly, rubbing Jack’s belly with one hand, the other taking a hold of the kid’s slippery wet cock and pumping him slowly.  
  
Sam’s hand wraps around his, the other around the back of Jack’s neck, holding him there and looking him straight in the eye, “Let us in, baby,” he says, voice that soothing tone you use on frightened animals, “let us fill you right up, you trust us, don’t you?”  
  
Jack lets out a strangled sob as Dean comes to a stop, all the way inside the almost painfully tight clutch holding them, the solid heat of his brother’s cock alongside his own. The older man wants to speak, wants to soothe Jack, too, but his breath is stolen from him when muscles flutter and tighten, causing Sam’s hips buck entirely of their own volition.  
  
“Fuck,” Jack gurgles at the same time Sam mutters an apology, pulling his hand away from Dean’s on the kid’s cock and grabbing his shoulder, “ow, that’s...!”  
  
Dean freezes all over, “Are you OK?” he asks, urgently, needing to know they’ve not gone too far, “Is it too much?” there’s silence for an agonising few seconds, with the exception of their panting breaths and the pounding of Dean’s heartbeat.  
  
Jack takes a shaky breath, one hand slipping on Sam’s sweaty chest, the other reaching back to grip Dean’s thigh before he takes another breath and releases it. He makes a noise in the back of his throat as he moves his hips a fraction of an inch, muscles first clenching then relaxing. He wobbles slightly as he opens his legs wider where they’re bracketing the outside of Sam’s thighs, and arches his back, a broken moan slipping from his candy pink lips, “So...full…” he pants.  
  
“But is it too much?” Dean repeats, needing to know, ready to pull out if needs be.  
  
Jack shakes his head, drops of sweat running from his hairline down his neck, “Just give me a minute.”  
  
Sam swallows audibly and casts a worried look in Dean’s direction, “We can stop, Jack,” he says, rubbing his thumb over the kid’s neck in a soothing gesture, “we should have asked, we just wanted to fill you right up.”  
  
The Nephilim shakes his head again, the pressure around their cocks decreasing as he relaxes a little, “I didn’t know you could…” he pants, slowly rolling his hips and causing all three of them to gasp at the slide, “how is this possible?” he asks, the wonder clear in his voice.  
  
“You’d be amazed what’s possible when it comes to sex,” Dean says around a smirk, earning himself a raised eyebrow from his brother, “Don’t worry, sweetheart, there’s still plenty we can teach you.”  
  
“ _Dean_ ,” Sam grits out, “really not the time,” there’s sweat beading on his upper lip and in the hollow of his throat, no doubt from the effort of holding back from moving like he wants to, “Jack,” he says, softer now, “I’m gonna pull out, OK? We can try anoth-”  
  
He’s cut off by Jack’s loud, “NO,” and the kid’s hand moving from Sam’s chest to his bicep, the other releasing the grip on Dean’s thigh in favour of hooking around the back of his neck, the position pushing his shoulders closer to Dean’s chest, “Just go slow,” he says.  
  
Sam looks between the two of them, “Shall I move?” he asks, voice a little uncertain.  
  
Jack nods, threading his long fingers into the sweaty hair at the nape of Dean’s neck, nails scrabbling along his scalp when Sam thrusts, punching out a grunt out of the kid’s mouth even though there’s barely any force behind it.  
  
“OK?” Sam asks, his breathing carefully measured as he fucks their boy at a painfully slow pace.  
  
Jack’s answer is a groan because Dean chooses that moment to resume slowly pumping the Nephilim’s still hard shaft, thumbing the head, spreading his slick around to make the glide smoother, “So fucking wet, kid, you love being stuff so full, don’t you?” he rasps.  
  
“Y-yes,” he says, his words and hips stuttering as Dean begins to thrust.  
  
Dean’s had a lot of sex over the years, with Sam and with other people but right here and now, he’s never felt anything quite like it. He keeps his movements slow at first, moaning at the feeling of such a hot, tight space and the feeling of Sam’s cock sliding hot and hard against his as they work their hips almost in opposition so that there’s friction for both of them and Jack’s constantly kept filled.  
  
The only sounds in the room for what could be minutes or hours is their breathing and moans, the slick sounds of lube and of Dean’s hand working Jack’s cock, until Sam starts to make urgent sounds in the back of his throat.  
  
“Shit,” he says, “I’m getting close, Jack….hngh, can I move quicker?” Their boy lets out a loud groan in response, working his hips faster on their cocks, his breath hitching when Sam takes it as a yes and fucks up into the slim body harder and faster.  
  
“Jesus,” Dean moans at the glorious friction and the rhythmic squeezing of Jack’s muscles as he moves, “Jack, I don’t know how much longer I can hold out,” he rasps, tightening his grip on the kid’s hip which must surely bear bruises in the shape of his fingers, already.  
  
“Do it,” Jack whimpers, “fuck me harder.”  
  
Sam grunts and speeds up, hips working faster and harder, the sound of skin slapping against skin getting louder as he does, “Gonna let us both come inside you again, baby?” he manages around heaving breaths, “Put it all up inside you so deep it’ll be leaking out all day?”  
  
“Fuck, Sam,” Dean groans at the words, his brother’s sense of urgency now creeping into him as his own hips work faster, trying to keep a rhythm going but all three of them are working at different paces now, “you do want that, right, Jack?” he says, working his hand faster, needing to feel the boy come around them.  
  
Needy little whimpers fall from Jack’s lips as he tries to speak, “Y-y-eah,” he manages, groaning when Sam shouts out before stilling, his cock twitching against Dean’s, coming hard, wet heat making the slide easier as the older man fucks into their boy harder and deeper. He winces as Jack’s nails dig into his scalp, letting out a strangled cry as his whole body arches, coming all over the hunter’s hand and his own chest and belly.  
  
“Oh fuck, oh fuck,” Dean chants, chasing his own orgasm, Sam cock still twitching against him while Jack’s muscles tighten and flutter around them both. He moves both hands to Jack’s hips, pulling him closer as he pounds into the kid, feeling and hearing the sound of his brother’s load leaking out of Jack’s hole and over Dean’s balls until the tension snaps and finally he comes with a shout, muffled by where his face is buried in the side of Jack’s neck.  
  
He’s not sure he didn’t black out for a moment because when he comes back to awareness Jack is collapsed on Sam’s chest, pressing sloppy kisses to his chin while Sam rubs the kid’s back. Dean’s fingers are numb where he’s been gripping Jack’s hips but he manages to unclamp them, the slender body sliding a little lower when he does, two matching grunts as Sam slips out of Jack with a wet sound. Despite wanting nothing more than to collapse on top of his two lovers Dean somehow manages a few more thrust into Jack’s abused hole, riding out the aftershocks, feeling more wet heat slide out of the kid with every movement, fucking their come slowly out of him. That won’t do, so Dean slides two fingers through the sticky mess dribbling down Jack’s thighs and pushes it back inside as deep as he can. He watches as the kid’s gaping hole flutters, trying to grip the fingers pushing into him but not quite reaching because of how stretched he is at the moment, and _fuck_ there’s something about that that Dean finds so hot. When their boy whimpers at the overstimulation he finally pulls out, collapsing to the side, wrapping his arm around Jack’s lower back and his brother’s waist at the same time.  
  
“You OK, baby boy?” Sam asks, quietly. When there’s no answer he tries again, “Jack?”  
  
The sound of muffled sobs makes Dean’s blood run cold, and despite the ache in his body and not having caught his breath yet he sits up, both his and Sam’s hands pushing the boy up from Sam’s chest so they can see his face.  
  
“Jack, come on,” Dean says, hearing the desperation in his own voice. He cups the Nephilim’s chin and lifts his head, heart stuttering in his chest when tears pour down young cheeks, “Oh shit, I’m so sorry, sweetheart!” he says as his stomach clenches.  
  
Sam pushes himself up on his elbow, in turn forcing Jack to sit up a little and cups their young lover’s cheek, “Jack, talk to us, please,” he says, breath hitching in a way Dean recognises as the start of panic.  
  
Jack takes a deep, shaky breath and slowly blinks his eyes open, reaching out with unsteady arms to cup both of their faces and offers them a small smile, “I’m alright,” he sniffles, “just a little...it was pretty intense but I’m OK, promise.”  
  
Sam’s sigh of relief is loud in the room as he flops back onto the bed, throwing one arm over his face.  
  
“You had us scared, there, kiddo,” Dean says softly, pushing up to place a gentle kiss to Jack’s lips, tasting salty tears, then the kid’s own flavour as he lazily pushes his tongue into the older man’s mouth, both letting out a soft sigh when they break apart.  
  
“Hey, what about me?” Sam says, trying to sound offended but there’s too much of a smile in it to be anything other than teasing. Jack leans down unsteadily to kiss him, too, before he all but collapses over both of them.  
  
Dean shifts closer so the side of Sam’s body is moulded along the length of his and presses a soft kiss of his own to his brother’s lips.  
  
“Sleepy,” Jack murmurs, letting his head rest on Sam’s shoulder and looping an arm around Dean’s waist to hold him close.  
  
They all shift to get into a more comfortable position to ride out the afterglow, Sam somehow pulling up the sheet to cover them all, and soon Dean feels sleep drawing him under until Jack speaks again.  
  
“I think I’d like you to hold me up next time, Dean, that way I can wrap my arms and legs around you. I know how much you like me doing that.”  
  
Sam doesn’t open his eyes but keeps slowly stroking Jack’s back and when Dean glances over to him there’s a smile on his brother’s face. The older Winchester looks back to meet Jack’s gaze, “What makes you think there’s gonna be next time, huh, kid?” Deans says, trying to sound like he doesn’t care one way or another even though there’s a zing of fresh arousal down his spine at the thought of it.  
  
“There will be,” Jack replies, knowing blue eyes twinkling with mischief despite the fucked out tiredness making his lids heavy, “you always give me what I want...you both do.” he says around a small yawn.  
  
Dean wants to deny it but they all know it’s true, “When did you become such a little bitch? Sammy, this is all your fault!” he snips, sounding as disgruntled as possible even though he can’t help the fond eye roll.  
  
“Go to sleep, jerk.” Sam replies around a laugh.  
  
Jack’s happy, sleepy smile is the last thing he sees before they all drift off.


End file.
